Sodium Carbonate → Ethyl 4-(1,5-dimethyl-1H-pyrazol-4-yl)-6-methyl-2-(methylthio)pyrimidine-5-carboxylate

HRID 2092796ノート

反応式

HRID 2092796 の反応式
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1.[CH3:16][N:17]1[C:21]([CH3:22])=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[N:18]1.C(=O)([O-])[O-].[Na+].[Na+]>CC(N(C)C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:16][N:17]1[C:21]([CH3:22])=[C:20]([C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=2)[CH:19]=[N:18]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 22225416Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylateHCID 426473131,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

生成物 1

HCID 58317629Ethyl 4-(1,5-dimethyl-1H-pyrazol-4-yl)-6-methyl-2-(methylthio)pyrimidine-5-carboxylate収率 71.5%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
80 °C

実験手順

Ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate (0.179 g, 0.726 mmol), 1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.242 g, 1.088 mmol), and PdCl2(dppf) (0.106 g, 0.145 mmol) were dispersed in DMA (2 mL). After 10 min, 2 N sodium carbonate (1.814 mL, 3.63 mmol) was added to the reaction mixture. The reaction mixture was purged with nitrogen, sealed in a vial, and then heated at 80° C. for 5 h. The mixture was subsequently filtered through a pad of Celite, rinsed with MeOH, and the filtrate was purified via reverse phase preparative HPLC. The fractions were concentrated in vacuo to give the title compound as tan needles (0.159 g, 71%). [M+H] calc'd for C14H18N4O2S, 307; found, 307.

後処理

  1. customThe reaction mixture was purged with nitrogen
  2. customsealed in a vial, and
  3. filtrationThe mixture was subsequently filtered through a pad of Celite
  4. washrinsed with MeOH
  5. customthe filtrate was purified via reverse phase preparative HPLC
  6. concentrationThe fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-365ae6d006e84b17a4a9dc5e464d0e61
出典データセット
uspto-grants-2013_05
特許番号
US08440689B2

反応ノート

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